Plant growth regulators

ABSTRACT

N-substituted long-chain alkenyl succinimides are useful plant growth regulants.

United States Patent 11 1 Abramitis et al.

1 1 PLANT GROWTH REGULATORS [75] Inventors: Walter William Abramitis, Downers Grove; John J. Callahan, Park Ridge, both of 111.

[73] Assignee: Akzona Incorporated, Asheville,

[22] Filed: Apr. 13, 1973 [21] Appl. No.: 350,854

[52] US. Cl 71/76; 71/95; 260/3265 FM [51] Int. Cl AOln 9/22 [58] Field of Search 71/76, 95; 260/3265 F, 260/3265 FM [56] References Cited I UNITED STATES PATENTS 2,865,730 12/1958 Gates et a1 71/95 3,240,799 3/1966 I-Iageman et al.. 71/76 6/1966 Hageman et a1 71/76 1 May 13, 1975 OTHER PUBLICATIONS Forbes et al., AshFree Antiflocculant N-Aminoalkenyl etc.," (1971), CA 74 No. 10142521.

Primary ExaminerG1ennon H. Hollrah Attorney, Agent, or Firm--Francis W. Young; Philip M. Pippenger 57 ABSTRACT N-substituted 10ng-chain alkenyl succinimides are 11seful plant growth regulants.

6 Claims, No Drawings 1 PLANT GROWTH REGULATORS SUMMARY OF THE INVENTION This invention is related to plant growth regulators and particularly those which selectively stimulate growth or retard growth to obtain increased yields, de' pending upon the concentration and time of application of the regulators and upon the particular species of plants being treated.

BACKGROUND OF THE INVENTION Various derivatives of succinic acid have been proposed as plant growth regulants and herbicides. The proposed derivatives include succinic acid (U.S. Pat. No. 3,399,990) (as a herbicide), decenyl-N, N-dimethyl-succinic acid (Chem. Abst. Vol. 67, page 99099g), succinamides (U.S. Pat. No. 3,632,646), succinamates (Canadian Pat. No. 861,554), N-substituted succini' mides (U.S. Pat. No. 2,992,223) (a herbicide), N phenyl-substituted succinimides (U.S. Pat. No. 3,538,114) (as a herbicide) and N-dimethylaminodecenyl succinimide (U.S. Pat. No. 3,578,679) (frost protection). In Example III of Canadian Pat. No. 861,554, data was presented indicating lack of any growth regulating effect of N,N-dimethyl beta-dodecenyl succinamic acid on flax seedlings. Other related prior art includes US. Pat. No.s 2,865,730 and 3,240,799.

DESCRIPTION OF THE INVENTION More particularly, the invention relates to the discovery that certain N-substituted long-chain alkenyl succinimides are useful in stimulating plant growth and/or obtaining increased yields. It is surprisingly found that growth can be stimulated or inhibited, i.e. dwarfed, depending upon the concentration of growth regulator applied and that the same regulator may have different effects upon different species. As a result of dwarfing, increased yields are obtained and furthermore, cultivation and harvesting of crops particularly by mechanical means is made easier.

The growth regulators of the instant invention can be applied to the seeds by soaking them in the growth regulator, to the soil or to the plant foilage in various stages.

I have found that certain alkenyl-substituted succinimides are effective in stimulating the growth of certain plant crops and inhibiting growth of the same crops depending upon the concentration of growth regulator used. In certain cases, growth is stimulated by application of the growth regulator in concentrations less than 500 parts per million (ppm.) and are inhibited by concentrations of 500 parts per million or greater.

Furthermore, the succinimides of the present invention may also be applied as the reaction product of an N-alkyl amine and an alkenyl succinic acid, for example, N-Z-undecylamine and dodecenyl succinic acid. The reaction products of the latter have been analyzed and found to contain the following four compounds: dodecenyl succinic acid; 2-undecylammonium-N-2 undecylododecenyl succinamate; N-2- undecylododecenyl succinimide and bis-(2- undecylammonium) dodecenyl succinate.

When spraying foilage, a surfactant was used to aid in emulsification of the regulant and increase absorption by the plants. Best results were obtained with equal volumes of plant growth regulator and surfactant although as little as 0.1 percent by weight of surfactant to growth regulator can be used. The particular surfactant is not critical and may be selected from wellknown commercially available materials such as Armotan PML-20 [an ethoxylated (20 moles ethyleneoxide) coconut fatty acid ester of sorbitan marketed by Armak Company] or X-77 (a proprietary mixture of surfactants marketed by Colloidal Products Inc.).

The compounds of the invention may be prepared by the reaction above described in the following manner:

Mix stoichiometric amounts of N-Z-undecylamine and dodecenyl succinic acid in a beaker in a nitrogen atmosphere. The mixture is heated to C and agitated for 4 to 8 hours.

The compounds may also be prepared from alkenyl succinic anhydrides as follows:

N-(undecyl) dodecenylsuccinimide was prepared by adding 8.56 g (0.05 mole) of N-undecylamine to 13.83 g (0.05 mole) of dodecenylsuccinic anhydride in 100 ml of Xylene in a round bottom flask with attached Dean-Stark trap and condenser. The mixture was heated to the boiling point and held there for 36 hours. After removal of the solvent, 21.9 of an amber-colored liquid was obtained. The liquid was washed with several portions of 5% aqueous hydrochloric acid and 5% sodium bicarbonate solution. Wet analysis indicated that no amine was present but that 0.149 meq. of carboxyl/g was present. The liquid was dissolved in a mixture of isopropanol and water and passed through an Amberlit IRA 400 anion exchanger. 2.35 g of liquid gave 1.6 g of product which contained no carboxyl and no amine and which showed a strong imide carbonyl absorption band in its infrared spectrum at 5.85;!"

Exemplary compounds falling within the invention include: N-l-undecylododecenyl succinimide; N-2- undecyl dodecenyl succinimide; N-( l-undecy1)-2,3- dimethyl succinimide; N( l-undecy1)-2,2-dimethyl succinimide; N(2-undecyl)-2,2dimethyl succinimide; brominated N-(1-undecyl)-doclecenylsuccinimide; N- (l-undecyl) octenyl succinimide; N-( l-undecyl) dece nyl succinimide and N-( l-undecyl) tetradecenyl succinimide, and have the following general structure:

wherein R is alkyl or alkenyl having from 8 to 22 carbon atoms; R R and R are H or CH;,, and R is alkyl or alkenyl having from 8 to 22 carbon atoms or H, if two of R, R or R are methyl.

The invention is further illustrated by the following examples.

EXAMPLE I Two species of beans in the two-leaf stage and emerging peas 1.5 inches in height were sprayed to runoff with N-(2-undecyl)-dodecenyl succinimide at concentrations 1,500 parts per million (ppm.) and ppm. The height of the plants was measured two days after spraying and again 13 days after spraying. The difference in height increase from the control is recorded in the last column of Table 1 below wherein a negative number indicates dwarfing.

TABLE I Ht. 2 days Ht. 13 days Increase Difference Plant Species Conc. (ppm) after spraying after spraying l 1 days from control Pinto Beans 1500 2.5 in in. 1.0 in. -025 in. Pinto Beans I50 2.5 3.5 l.0 -0.25 Pinto Beans (control) 2.5 3.75" L25" Green Beans I500 7.0 8.25" 1.25" l.50 Green Beans I50 5.25" 6.5 L25" l.50 Green Beans (control) 0 4.5 7.25" 2.75 Peas 1500 3.75" 10.5 6.25" 2.25 Peas 150 4.0 12.0 "-8.00" o.50 Peas (control) 0 3.5 l2.0 8.50"

EXAMPLE 11 TABLE 111 Peppers at the seedling stage, snapdragons at the 15 New growth Difference seedling stage and petunias at the pre-bud or seedling during 9 from stage were sprayed to runoff with the same regulant Plant Species Conc.(ppm) days after Control used in Example I at a concentration of 2000 ppm. bpmymg The increase in growth during the nine days following Pepper 2000 2.12 in. l.63 in. spraying was recorded and compared to control plants ggfi gi 8 r having no treatment. The treated pepper plants aver- Petunias (control) 0 4.02 aged 2 inches of new growth during this period while m ig i 7000 S N v the control plants averaged 3.75 inches of new growth. Navy Beans (control) 0 5.50

Growth was retarded by 1.75 inches by the application of N-(Z-undecyl) dodecenyl succinimide to pepper EXAMPLE IV plants. Similar results were obtained by treatment of N (l undecyl) dodecenyl succinimide was applied in the other specles as hsted below m Table the same matter as Example II to peppers, petunias and Michigan Navy White Beans. Results are shown in Table IV.

TABLE IV TABLE H New growth Difference during 9 from Newgrowth Difference Plant Species Conc.(ppm) Control during 9 from Plant Species Cone. (ppm) days after Control Pepper 2000 L88 in *P Pepper (control) 0 3.75

- Petunias 2000 4.50 0. l 2 Pepper 2000 2.00 in. l.75 in. Petunias (control) 0 4.62 Pepper (control) 0 3.75 New growth Snapdragons 2000 4.62 ().I3 40 during 7 Snapdragons 0 4.75 y Petunias 2000 3.88 -0.74 g m Na y spmymg Petunias (control) 0 4.62 white Beams 0000 2'88 2'62 White Beans (control) 0 5.50

EXAMPLE V N-( l-undecyl) -2,2-dimethyl succinimide was applied in the same manner as Example [I to peppers, EXAMPLE 1 snapdragons, petunias and Michigan Navy White Beans. Results are shown in Table V. On peppers, petuy dodecenyl Succmlmlde PP nias and Michigan Navy White Beans, the growth reguthe Same manner 35 Example H to P pp Petumas lant of this example retarded growth while growth was and Mlchlgan y whlte Beans- Results are Shown stimulated when the same regulant was applied to snap- Table III. dragon.

TABLE V New Growth Difference 9 days from Plant'Species Conc.(ppm) after spraying Control Peppers 2000 L88 in. I.87 in. Peppers (control) 0 3.75 Snapdragons 2000 5.25 +0.50 Snapdragons (control) 0 4.75 Petunias 2000 LOO -3.63 Petunias (control) 0 4.62 Michigan Navy White Beans 2000 3.50 2.00 White Beans (control) 0 5.50

EXAMPLE V1 TABLE '111 (ontmued N-( l-undecyl) -2, 3-dimethyl suc cinimide was ap- H d 'g l'j? plied in the same manner as Example 11 to peppers. S lrealmcnt ppm. growth 1111.1 (611111111111 1 snapdragons, petunias and Michigan Navy White Beans. Results are shown in Table VI. undecyl1- TABLE V] New Growth Difference during 9 days from Plant Species C onc.( ppm) after spraying Control Peppers 2000 1.62 in. 2.13 Peppers (control) 3.75 Snapdragons 2000 4.00 0.75 Snapdragons (control) 0 4.75 Petunias 2000 l .00 3.62 Petunias (control) 0 4.62 Michigan Navy White Beans 2000 1.25 -4.25 White Beans (control) (1 5.50

EXAMPLE v11 9!" succminnde When used on tomatoes in the same manner as in the 300 500 23.13 2.00 prevlous Examples, N-(Z-undecyl) dodecenyl succml- 19462 450 mide resulted in stimulation of growth. Nine days after 1.0 treatment new growth of 2.38 inches was recorded compared with 1.94 inches for the control. Other dodec enyl growth regulators of the invention also showed stimusuccmmde H 67 4 S1 lating effects on tomatoes as follows: E 1 6 j};

TABLE VI] Tomatoes New Growth Difference during 9 days from Chemical Conc.(ppm) after spraying Control N-(2-undecy1)dodecenyl succinimidc (see Example 11) 2000 2.38 in. +0.44 in. N-( l-nonyl) dodecenyl succinimide (see Example 111) 2000 2.62 +0.68 N-( l-undecyl) dodecenyl succinimide (see Example 1V) 2000 4.00 +2.06 N-( l-undecyl) 2, Z-dimethyl succinimide (see Example V) 2000 3.12 +1.18 N-( l-undecyl) 2, B-dimethyl succinimide (see Example VI) 2000 2.50 +0.56 Control, no treatment 0 1.94

EXAMPLE V111 15.00 -0.12 5 1,000 Other succmtmides of the 1nvent1on were apphed to N-E Z- I U11 ecy navy beans growmg 1n the laboratory 1n the same mandodecenyl ner as the previous examples and the growth 1n Inches succinimidc recorded after 14 days. The results of treatment with spray concentrations at 200 ppm. 500 ppm. and 1,000 :5 5; ppm. are recorded in Table V111: 1,000 N-( l-nonyl) TABLE V111 dodecenyl succinimide Difference 200 17.00 -4. 1 3 14 day from 500 19.50 1 .63 Treatment ppm. growth (in.) Control (in.) 18.50 3.38

1,000 Control 200 21.13

500 21.13 undecy 15.12 tetradece- 1.000 y I N4 1. succmimide d l 200 17.00 4. l 3 a 500 19.50 -l.60 succinimide 13-50 16.50 1 .311 undecyr 1,000 2.2 14-1 1- dimethyl undecyl 1- succinimide nonenyl 200 15.62 5.51 succinimide 500 19.62 1.51 200 19.63 1 .50 16.00 0.88 500 22.13 1.00 1,000

21.75 6.63 1,000 undecy1)- TABLE Vlll-Continued Dilference l4 day from Treatment ppm. growth (in.) Control (in.)

2.3 dimethyl succinimide EXAMPLE lX A reaction product of N-2-undecylamine and dodecenyl succinic acid was prepared by mixing stoichiometric amounts of each in a beaker in a nitrogen atmosphere and heated to 120C with agitation for 4 to 8 hours. Analysis of the product showed the following percentages of solids (total 28.132 percent):

Dodecenyl succinic acid 0.342 7! Z-undecylammonium N-Z undecyl dodecenyl succinatate 7.8 N-(Z-undecyl) dodecenyl suc cinimide L64 Bis- (lundecylammonium) dodecenyl succinate 18.35

TOTAL 28.132 '/l The reaction product (both actual and reconstituted) was tested on a large variety of crops and caused increased growth in some instances and dwarfing, larger leaves, moreflowers and better seeds and fruit yield in others. -For example, alfalfa seed production was im proved by' 51.6 percent over the control when sprayed to runoff at 10 percent bloom stage with 2000 ppm. of the reaction product referred to in this example. Increased seed yield over the control was also obtained when the reaction product was applied at the same rate at the percent bloom stage, in two separate applications at the 10 and 25 percent bloom stage and in a single application at a rate of 4000 ppm. at the 25 percent bloom stage. The results are as follows:

In a field test on Alberta wheat, the reconstituted reaction product applied at a rate of one quart per acre, yield was increased by 123 pounds per acre or 8 percent. The reaction product sprayed on greenhouse rice at a rate of 1500 ppm. showed significant improvement in yield at low nitrogen level treated plants, although no improvement was observed at medium or high levels of nitrogen treated plants.

EXAMPLE X In greenhouse tests, Inia wheat in the panicle stage was sprayed to runoff with N-(Z-undecyl) dodecenyl succinimide at 1500 ppm. The total number of seed heads recorded was 63 compared to 49 for control plants.

I claim:

1. A method for increasing or decreasing plant growth comprising applying to the locus of a plant an effective amount of a regulant of the formula:

in which R is alkyl having 8 to 22 carbon atoms; R, is selected from the group consisting of hydrogen and alkenyl having 8 to 22 carbon atoms; R R and R are selected from the group consisting of hydrogen, methyl, and alkenyl having 8 to 22 carbon atoms: and when R 'is alkenyl, R R and R. are hydrogen. 2. The method of claim 1 wherein the regulant is N- (2-undecyl)-dodecenyl succinimide.

3. The method of claim 1 wherein the regulant is N- l-nonyl) dodecenyl succinimide.

4. The method of claim 1 wherein the regulant is N- (l-undecyl)-dodecenyl succinimide.

5. The method of claim 1 wherein the regulant is N- (l-undecenyl) 2,2-dimethyl succinimide.

6. The method of claim 1 wherein the regulant is N-( l-undecenyl)-2,3-dimethyl succinimide. 

1. A METHOD FOR INCREASING OR DECREASING PLANT GROWTH COMPRISING APPLYING TO THE LOCUS OF A PLANT AN EFFECTIVE AMOUNT OF A REGULANT OF THE FORMULA
 2. The method of claim 1 wherein the regulant is N-(2-undecyl)-dodecenyl succinimide.
 3. The method of claim 1 wherein the regulant is N-(1-nonyl) dodecenyl succinimide.
 4. The method of claim 1 wherein the regulant is N-(1-undecyl)-dodecenyl succinimide.
 5. The method of claim 1 wherein the regulant is N-(1-undecenyl) 2,2-dimethyl succinimide.
 6. The method of claim 1 wherein the regulant is N-(1-undecenyl)-2,3-dimethyl succinimide. 